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Bolivian Journal of Chemistry
Received 12 13 2016
Accepted 12 21 2016
Maldonado et Al.
2Department
of Biology, Ecology Institute IE, National Herbarium of Bolivia LPB, Universidad Mayor de San
Andrs UMSA, P.O. Box 10077, Calle Andrs Bello s/n, Ciudad Universitaria Cota Cota, Phone 59122792582,
La Paz, Bolivia, lpb@acelerate.com
3Department
Spanish title: Presencia de atranorina en Physcia sorediosa. Reportamos la presencia del depsido
denominado atranorina en el liquen Physcia sorediosa (Physciaceae) mediante su aislamiento y caracterizacin por
RMN, el liquen fue colectado en el campus Universitario de Cota-Cota, UMSA, La Paz Bolivia.
INTRODUCTION
Lichens are vegetal organisms generated by the symbiosis of algae and mushrooms [1]. They synthesize secondary
metabolites as depsides, terpenoids, acids, quinones, chromones, xanthones and anthraquinones [2]. In our study of
the lichen Physcia sorediosa, collected in the main campus of UMSA in La Paz (3600 m.a.s.l.), we have isolated the
depside atranorin 1, see Figure 1. The structure was assigned by analysis of the 1H NMR and 13C NMR data of
compound 1 (Fig. 2 and 3, Table 1) in comparison with those published in the literature for atranorin [3].
1
Figure 1. The depside atranorin 1, characterized in the lichen Physcia sorediosa
175
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Accepted 12 21 2016
Maldonado et Al.
HO-4
HO-2 HO-3
8
65
Figure 2. 1H NMR spectrum of 1, 300 MHz, CDCl3, from TMS. Molecular drawing with
numbering system extracted from Carvalho et al. [3], authorization pending from JBCS.
Atom
1
2
3
4
5
6
7
8
9
1
2
3
4
5
6
7
8
9
CH3O
HO-2
HO-4
HO-3
1a
1 H
6.39 s
10.37 s
2.71 s
6.54 s
2.11 s
2.56 s
4.00 s
12.52 s
12.57 s
11.95 s
EXPERIMENTAL
General
The NMR spectra were run in a Bruker DRX300, (300 MHz 1H, 75 MHz 13C) equipment at the Department of
Chemistry of UMSA.
Vegetal material
Physcia sorediosa was collected at the main Campus of Major San Andres University (UMSA) at 3600 m.a.s.l. (La
Paz, Bolivia) in December 2005, the material was identified in the National Herbarium of Bolivia (LPB).
Extraction and isolation
The plant material was selected, cleaned, dried and milled, it weighed 10.1 g. 10.1 g of dried material was extracted
with acetone during 48 h. at room temperature. The filtrate was concentrated at reduced pressure and once dried it
was crystalized in ethanol-dichloromethane (1:1) to afford a white crystalline solid or compound 1 (0.6 g, 5.94%).
Downloadable from: Revista Boliviana
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Accepted 12 21 2016
Maldonado et Al.
Peakpicking
24
3 1 6
9 9
CH3O
65
5
2
7 7
3
4
Figure 3. 13C NMR spectrum of 1, 75 MHz, CDCl3, from TMS. Molecular drawing with
numbering system extracted from Carvalho et al. [3], authorization pending from JBCS.
Table 1. Comparison of 1H and
different vegetal sources
Atom
1
2
3
4
5
6
7
8
9
1
2
3
4
5
6
7
8
9
CH3O
HO-2
HO-4
HO-3
aPhyscia
Compound
1a
1 H
6.39 s
10.37 s
2.71 s
6.54 s
2.11 s
2.56 s
4.00 s
12.52 s
12.57 s
11.95 s
13C
Atom
1
2
3
4
5
6
7
8
9
1
2
3
4
5
6
7
8
9
CH3O
1b
1H
6.39 s
10.30 s
2.67 s
6.50 s
2.07 s
2.53 s
3.97 s
12.49 s
12.54 s
11.94 s
1a
13C
102.8 s
169.1 s
108.5 s
167.5 s
112.8 d
152.4 s
169.7 s
193.0 s
25.6 q
152.4 s
116.8 s
162.9 s
110.2 s
139.9 s
116.0 d
172.2 s
9.4 q
24.0 q
52.3 q
1b
13C
102.8 s
169.1 s
108.5 s
167.5 s
112.8 d
152.4 s
169.7 s
193.8 s
25.6 q
152.0 s
116.7 s
162.8 s
110.3 s
139.9 s
115.9 d
172.2 s
9.4 q
24.0 q
52.3 q
sorediosa, (300 and 75 MHz, CDCl3); bOuratea floribunda [3], (400 and 100 MHz, CDCl3)
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1a
13C
102.8 s
169.1 s
108.5 s
167.5 s
112.8 d
152.4 s
169.7 s
193.0 s
25.6 q
152.4 s
116.8 s
162.9 s
110.2 s
139.9 s
116.0 d
172.2 s
9.4 q
24.0 q
52.3 q
Accepted 12 21 2016
Maldonado et Al.
ACKNOWLEDGEMENTS
Authors wish to thank Dr. Yonny Flores Segura, Laboratory of NMR, Department of Chemistry, UMSA for the
recording of NMR spectra. The Research Institute of Natural Products (IIPN) is acknowledged for financial support.
REFERENCES
1.
2.
3.
4.
5.
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Journal
178
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